The Original Queens of the Red Carpet

If award show newbies need inspiration for the impending awards show season, there's a smarter source than Rachel Zoe and company. The new guard should turn to the few true originals who still break fashion rules (yet still own their looks) whenever the flashbulbs pop.

"There are two points in your life when you can take risks: when you're very young, and when you're older, because you've lived through everything," says celebrity stylist Phillip Bloch. "Those women are kind of 'been there, done that.'"

In his forthcoming book, "The Shopping Diet" Bloch celebrates women of a certain age who choose to grow old disgracefully. "She's the kind of woman who has traveled the world, and picks up things along the way so they become part of who she is. It's not just her wardrobe but her medals of honor." These women are more devil-may-care than "Devil Wears Prada."

"Anytime a woman expresses who she is on the red carpet, I applaud it," adds Rob Zangardi, whose client roster includes Rihanna and Rachel McAdams. "And these women who don't play it safe? They're an inspiration to the younger stars to take chances. And as a stylist, I appreciate that." (Translation: maybe Zangardi won't have to call in so many snooze-inducing LBDs next year.)

This awards season, some of the prissier Fashion Police may class these women as repeat offenders, but the red carpet would be dull without them (not to mention that Joan Rivers and co. would be out of a job). It may be easy to pillory fashion risk takers of a certain age, but it's through visionaries – whether YSL's trouser suit or Rudi Gernreich's monokini - that fashion advances.

Sure, the actress wore Miuccia Prada's namesake line when hyping the smash fashion film, "Devil Wears Prada," but to her, clothes are simply a costume for characters. When she's playing Meryl Streep, she'll wear whatever is clean and available.

"She doesn't need any fashion validation at all – Meryl gains all of her confidence from her art, her skills, the fact she's a great actor," says stylist Rob Zangardi. "Her closet's probably too full of Oscars to make room for extra heels and bags."

Swinton's fashion choices are as unconventional as her ménage-a-trois private life. The statuesque redhead – who astonishingly turns 50 next year - "is such a fashionista intellectual. She's what I call a fashion sob saying 'I'm not into fashion'" Bloch observes. The key to Swinton's style: she isn't afraid to fail. "Tilda is one of my fashion favorites – not only does she wear clothes really well, she also always looks impeccable," Zangardi counters, before confiding "Designers absolutely love her."

Actress Tilda Swinton attends the "South Of The Border" Premiere during the Venice Film Festival on September 7, 2009.

Her humorist brother David may talk of dressing his family in corduroy and denim, but doubtless Amy would opt out. The off-kilter comedienne, known for scene-stealing cameos, baking cupcakes, and being David Letterman's favorite guest, dresses like a cast member of 'Mad Men' with a dash of circus clown.

"She's inspired by a kooky 50s housewife," laughs Zangardi. "And she never fails to dress the part."

Actress Amy Sedaris attends the premiere of "Sex and the City: The Movie" at Radio City Music Hall on May 27, 2008 in New York City.

Ageless Italian fashionista Piaggi is such an original she's almost impossible to describe: a voracious vintage collector, muse to designers from Karl Lagerfeld to Manolo Blahnik, and an obsessive hat-wearer.

"She is all about the hats," Bloch notes, "I call her a fashion savant."

Indeed, Piaggi is never spotted in the same outfit in public twice. And she's certainly hard to miss with her dayglo makeup and fierce ensembles.

Anna Piaggi attends the Milan International Furniture Fair on April 22, 2009.

Not many women can claim to have a must-have purse named in their honor, as Birkin can. Way back when, the chairman of Hermès named a bag for the gap-toothed beauty after he saw her struggle onto a plane with too many purses.

Legendarily trend-resistant, the 62-year old Birkin remains an original, committed to the same style she developed as a teenage nymphet. "She's just got that hippie free spirit," Bloch says.

"She oozes sexuality and just uses her clothes to further that," Zangardi explains. "She has always taken fashions risks, which I love."

Cher's outfits may veer wildly from Oscar- to Razzie-worthy, but her unflappable cool means Mackie and co's sequins always sparkle – and she remains an original, standing apart.

"The thing about her? She's got the attitude, and she has a butchness and toughness that counteracts all the glamour and beads," raves Philip Bloch. "Some girls, like Toni Braxton God bless her, can take a $1000 dress and make it look $10, and some girls do the opposite."

Zangardi has first-hand experience of just how unusual she is, having worked with Lauper on shoots. He believes her refreshingly eccentric style to was due to the emerging New York club scene in the 1980s. "It was when artists took more risks – there were no articles judging "Who Wore It Better?" (Pity that's not a part of the '80s revival.)

Joie de vivre is crucial to Lauper's look and her legendary originality. "Her song says it all – girls just want to have fun," says Bloch. "She always looks the same but somehow completely different."

Singer Cyndi Lauper at the 51st Annual Grammy Awards in Los Angeles on February 8, 2009.

The Oscar-winning Brit has her own distinctive style: flowing, caftan-inspired shifts that are as much rural pottery teacher as red carpet regular. She clearly prizes comfort over trend-chasing, and is a true original for shunning international designer names.

Instead, Dench picks up most of her relaxed ensembles from a British boutique chainlet, Hampstead Bazaar. She's such a loyal fan, she's even unofficially endorsed the retailer. "When I'm in a panic and in a hurry to go out, I can't go wrong if I wear a dress from Bazaar," Dench has said.

Dame Judi Dench at Sir Elton John's White Tiara Ball in London on June 27, 2002.

Zangardi says that Dolly has the same savvy as Cher – the wardrobe equivalent of a wink that tells us she's in on the lurex-trimmed joke, her humor an original touch among the po-faced fashion crowd. "Cher is the posted child for glamour and Dolly does the same thing in a country-ish way," says Bloch. "She is a caricature of what we think she is and she does it for us."

Dolly Parton attends the 63rd Annual Tony Awards in New York City on June 7, 2009.

Like Birkin, flower child Nicks has a time-warpish vibe, still dressing now in the gypsy velvets from Fleetwood Mac's heyday. "I love it, and I love her because she's committed to who she is," says Bloch.

Though he might have an ulterior motive. "That's my period. She reminds me of the girls I dated in Junior High, with the braid down the side."

Singer Stevie Nicks performs on "The Today Show" in New York City on September 28, 2005.